Software Engineer, Pilot
$138-186k
+ Equity
More information about location
3 days a week in office
Bookkeeping services for startups
Be an early applicant
Bookkeeping services for startups
201-500 employees
Be an early applicant
$138-186k
+ Equity
More information about location
3 days a week in office
201-500 employees
Company mission
To help small businesses and startups to achieve their commercial goals by taking care of the CFO services, tax preparation and bookkeeping.
Role
Who you are
- 3+ years of experience as a software engineer
- Experience building production software and shipping customer-facing or business-critical systems
- Strong coding fundamentals and the ability to write clean, maintainable, well-tested code
- Good product and systems judgment, especially in ambiguous or evolving problem spaces
- Strong communication skills and comfort working cross-functionally
- Interest in building automation systems that are reliable, observable, and secure
- A thoughtful approach to building systems that are trustworthy, practical, and effective in production
- Even if you don’t have experience with every part of our stack, we’d still love to talk
Desirable
- Experience with Python in production
- Experience with workflow orchestration, automation platforms, or distributed systems
- Familiarity with agentic or AI-assisted systems in production environments
- Experience building observability, alerting, or operational debugging tools
- Experience with system security, permissions, or handling sensitive data
- Experience building evaluation or quality measurement frameworks
- Experience with fintech, accounting, or financial operations tooling
- Experience integrating with third-party APIs and external systems
What the job involves
- As a Software Engineer on the team, you’ll build product and platform capabilities that help transform financial data into dependable bookkeeping outcomes
- You’ll work closely with engineers, product managers, designers, and operational experts to ship systems that are practical, measurable, and robust
- This is a strong fit for someone who enjoys building real-world automation systems and is excited about the engineering challenges that come with agentic workflows, including orchestration, security, evaluation and observability
- Pilot’s backend is written in fully typed Python, and our frontend stack includes JavaScript, TypeScript, and Vue.js
- We use Terraform to manage infrastructure, deploy containerized services on AWS, and rely on Postgres and modern observability tooling in production
- Build, test, and deploy software in a continuous manner
- Develop systems that power bookkeeping automation, including agentic workflows and integrations with third-party platforms
- Design and implement reliable workflow orchestration across services, tools, and operational processes
- Build observability into automation systems so teams can understand performance, investigate failures, and improve quality over time
- Contribute to the security and reliability of systems that handle sensitive financial data and operational decisions
- Help design and improve evaluation frameworks that measure workflow quality, correctness, and business impact
- Partner with PMs, designers, and cross-functional stakeholders to turn ambiguous problems into practical solutions
- Write clear technical designs, contribute thoughtful code reviews, and maintain high engineering standards
- Investigate production issues, improve system reliability, and support services as needed
Our take
Back office operations such as bookkeeping can be an unwelcome distraction and expense for businesses. Pilot is the largest provider of back office services for startups and small businesses in the US, aiming to take care of a company's back office so they can focus on their core activities.
Founded in 2016. Pilot has attracted an impressive range of customers including Bolt, r2c and Pathrise. The company's proposition is more than just bookkeeping software, providing services that would ordinarily be provided by a fractional CFO. This empowers small businesses and startups to make better budgeting and spending decisions without the need of an expensive finance department hire.
The company evidently excels in customer service, with the vast majority of its business driven by customer referrals and organic interest. Going forward, Pilot aims to become to startups and medium-sized firms what AWS is to cloud computing - a comprehensive, easily scalable solution that prevents the need to reinvent a necessary but non-core function from scratch.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
-4% employee growth in 12 months
Company
Funding (last 2 of 5 rounds)
Mar 2021
$40m
SERIES C
Jan 2021
$60m
SERIES C
Total funding: $158.3m
Company benefits
- Development opportunities & employee happiness initiatives
- Seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox)
- Flexible vacation/time-off policy
- All federal holidays are observed
- Wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
- Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
- 401(k) plan
Company HQ
Financial District, San Francisco, CA
Leadership
Waseem Daher
(Chair & Co-Founder)They studied at MIT before founding Ksplice, where they spent 3 years as COO, and working at Oracle and Dropbox. Having founded Zulip in August 2012, they co-founded Pilot in January 2017.
Jessica McKellar
(CEO & Co-Founder)Previously, they were the founder and the VP of Engineering for a real-time collaboration startup acquired by Dropbox, where they then served as a Director of Engineering.
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